磺胺甲基嘧啶 | 127-79-7

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 磺胺甲基嘧啶
• 中文别名: 磺胺甲嘧啶
• 英文名称: sulfamerazina
• 英文别名: sulfamerazine；4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide；sulphamerazine；SMR；4-amino-N-(4-methyl-2-pyrimidinyl) benzenesulfonamide；2-sulfanilamido-4-methylpyrimidine；Sulfamerazin
• CAS: 127-79-7
• 化学式: C₁₁H₁₂N₄O₂S
• mdl: MFCD00023212
• 分子量: 264.308
• InChiKey: QPPBRPIAZZHUNT-UHFFFAOYSA-N

物化性质

• 熔点：
  234-238°C
• 沸点：
  519.1±52.0 °C(Predicted)
• 密度：
  1.3364 (rough estimate)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid
• 碰撞截面：
  156.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 保留指数：
  2573

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

ADMET

代谢

磺胺增效剂已知的人体代谢物包括N(4)-乙酰磺胺增效剂。

Sulfamerazine has known human metabolites that include N(4)-Acetylsulfamerazine.

来源:NORMAN Suspect List Exchange

吸收、分配和排泄

• 吸收

口服给药后迅速吸收。

Rapidly absorbed following oral administration.

来源:DrugBank

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  2935009090
• RTECS号：
  WP0750000
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  库房应保持通风、低温和干燥的环境。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Sulfamerazine
CAS-No. : 127-79-7
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37 Wear suitable protective clothing and gloves.
Other hazards
Possible sensitizer.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide
N1-(4-Methylpyrimidin-2-yl)sulfanilamide
Formula : C11H12N4O2S
Molecular Weight : 264,30 g/mol
Component Concentration
Sulfamerazine
CAS-No. 127-79-7 -
EC-No. 204-866-2

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
Nausea, Vomiting, Diarrhoea, Headache, Dizziness, Rash, Cyanosis
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Light sensitive.
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Impervious clothing., The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 233 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 0,728
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Reproductive toxicity - rat - Oral
Paternal Effects: Spermatogenesis (including genetic material, sperm morphology,motility, and count).
Reproductive toxicity - mouse - Oral
Effects on Newborn: Other neonatal measures or effects.
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
Nausea, Vomiting, Diarrhoea, Headache, Dizziness, Rash, Cyanosis
Additional Information
RTECS: WP0750000

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Section 12. ECOLOGICAL INFORMATION
Toxicity
Toxicity to fish LC50 - Morone saxatilis - > 100 mg/l - 96 h
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

生物活性

Sulfamerazine (RP 2632) 是一种磺胺类抗菌药。

靶点

• 抗生素作用

体外研究

Sulfamerazine 在水中表现出双指数衰减，在环糊精溶液中则表现为三指数衰减。在复合物中，其显示出显著的高场偏移，表明苯胺环深深封闭在 CD 空腔内。

体内研究

• Sulfamerazine 导致新生小羊浓度-时间曲线上显著变化的年龄函数曲线，这有力地说明了出生后第一周小羊有缺陷的吸收率。
• 在大鼠中，Sulfamerazine 显著延长了雌性仓鼠的寿命，并使其体重增加。喂食 Sulfamerazine 的大鼠比对照组达到了更高的最大体重。

用途

• 医药中间体
• 作用类似于磺胺嘧啶，但对由溶血性链球菌和肺炎球菌引起的感染具有较高的疗效。
• 适用于治疗肺炎、丹毒、脑膜炎等疾病。吸收较快，毒性较小。

类别与性质

• 类别：有毒物品
• 毒性分级：中毒
• 急性毒性：
  • 皮下注射（大鼠）LD50: 1890 毫克/公斤
  • 腹腔注射（小鼠）LD50: 1400 毫克/公斤
• 可燃性危险特性：可燃；燃烧时产生有毒氮氧化物和硫氧化物烟雾
• 储运特性：需在库房通风、低温干燥的条件下储存与运输
• 灭火剂：干粉、泡沫、砂土、二氧化碳，或使用雾状水

反应信息

• 作为反应物：
  描述：

  磺胺甲基嘧啶 在 盐酸 作用下， 生成 1-butyl-5-[4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-biguanide; sulfate
  参考文献：
  名称：

  Srinivas et al., Journal of the Indian Institute of Science, Section A, 1953, vol. 35, p. 47,50

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-4-甲基嘧啶 在 吡啶 、 sodium hydroxide 作用下， 生成 磺胺甲基嘧啶
  参考文献：
  名称：

  N¹-Sulfanilylamino-alkyl-pyrimidines

  摘要：

  DOI：

  10.1021/ja01262a034

文献信息

• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2019199979A1

  公开（公告）日：2019-10-17

  The present application provides compounds of formula: Methods of using these compounds for killing bacterial growth and treating bacterial infections are also provided.

  本申请提供了以下化合物的公式：还提供了使用这些化合物杀灭细菌生长和治疗细菌感染的方法。
• Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects
  作者：Ling-Ling Chiang、Ing-Jy Tseng、Pen-Yuan Lin、Shiow-Yunn Sheu、Ching-Tung Lin、Yun-Han Hsieh、Yi-Jing Lin、Hsiao-Ling Chen、Mei-Hsiang Lin

  DOI：10.3390/molecules21010100

  日期：——

  reaction of activated aziridine ring opening led to the discovery of a novel class of antitumor compounds. The analogues 10i-k, 11l-n, 12o-p, and 16q-s were obtained from treating cantharidinimide 6 and analogues (7, 8, and 13) with activated aziridines, which produced a series of ring-opened products including normal and abnormal types. Some of these compounds showed cytotoxic effects in vitro against

  合成了邻苯二甲酰亚胺衍生物5a-h，包括含有嘧啶基，吡嗪基，氢，噻唑基和恶唑基的磺胺酰胺。通过活化的氮丙啶开环反应来修饰邻苯二甲酰亚胺，导致发现了新型的抗肿瘤化合物。类似物10i-k，11l-n，12o-p和16q-s是通过用活化的氮丙啶处理邻苯二甲酰亚胺6和类似物（7、8和13）而制得的，这些化合物产生了一系列的开环产物，包括正常的和异常类型。这些化合物中的一些在体外对HL-60，Hep3B，MCF7和MDA-MB-231癌细胞显示出细胞毒作用。最有效的细胞抑制化合物N-cantharidinimido-磺胺二甲嘧啶（5a）具有抗HL-60和抗Hep3B细胞的活性。
• [EN] BIOREVERSABLE PROMOIETIES FOR NITROGEN-CONTAINING AND HYDROXYL-CONTAINING DRUGS<br/>[FR] PRO-FRAGMENTS BIORÉVERSIBLES POUR MÉDICAMENTS CONTENANT DE L'AZOTE ET DE L'HYDROXYLE
  申请人：BAIKANG SUZHOU CO LTD

  公开号：WO2015081891A1

  公开（公告）日：2015-06-11

  Disclosed are promoieties of the following formula which can be used to form prodrugs of nitrogen-containing or hydroxyl-containing drug or a pharmaceutically active agent: (I) and pharmaceutical compositions comprising the prodrugs.

  披露了以下公式的促销性质，它们可用于形成含有氮或羟基的药物或药物活性剂的的前药：(I)以及包含这些前药的药物组合物。
• SUGAR CHAIN-ATTACHED LINKER, COMPOUND CONTAINING SUGAR CHAIN-ATTACHED LINKER AND PHYSIOLOGICALLY ACTIVE SUBSTANCE OR SALT THEREOF, AND METHOD FOR PRODUCING SAME
  申请人：GLYTECH INC.

  公开号：US20150306235A1

  公开（公告）日：2015-10-29

  To provide a carrier linker that is capable of improving the water solubility of a physiologically active substance and more quickly releasing the physiologically active substance under specific conditions without utilizing light or enzymatic cleavage. [Solution]A novel sugar chain-attached linker comprising a sugar chain that is attached as a carrier.

  提供一种载体连接剂，能够提高生理活性物质的水溶性，并在特定条件下更快地释放生理活性物质，而无需利用光或酶解。【解决方案】一种新型的糖链连接剂，包括作为载体附着的糖链。
• [EN] TREATMENT OF INFECTIONS<br/>[FR] TRAITEMENT D'INFECTIONS
  申请人：ASCENDIS PHARMA AS

  公开号：WO2020064844A1

  公开（公告）日：2020-04-02

  The present invention relates among other aspects to a conjugate or a pharmaceutically acceptable salt thereof or a pharmaceutical composition comprising said conjugate or its pharmaceutically acceptable salt for use in a method of preventing or treating an infection, wherein said conjugate is water-insoluble and comprises a polymeric moiety -Z to which a plurality of moieties -L2-X0D-L1-D are covalently conjugated, wherein each -D is independently an antibiotic moiety; each -L1- is independently a linker moiety to which -D is covalently and reversibly conjugated; each -X0D- is independently absent or a linkage and each -L2- is independently either a chemical bond or a spacer moiety.

  本发明涉及一种共轭物或其药用可接受的盐，或包含所述共轭物或其药用可接受的盐的药物组合物，用于预防或治疗感染的方法，其中所述共轭物不溶于水，包括一个聚合物基团-Z，其中多个基团-L2-X0D-L1-D以共价结合方式共轭，其中每个-D独立地是抗生素基团；每个-L1-独立地是连接基团，与-D以共价和可逆方式结合；每个-X0D-独立地不存在或是一个连接，每个-L2-独立地是化学键或间隔基团。

表征谱图